Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
  • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
  • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/52—Amides or imides
  • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
  • C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2603/00—Systems containing at least three condensed rings
  • C07C2603/02—Ortho- or ortho- and peri-condensed systems
  • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
  • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
  • C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

Definitions

• This invention relates to fluorescent polymers and to monomer ingredients therefore.
• acrylamide polymers can be modified in aqueous solution with organic die molecules which can form stable carbo-cations reversibly in water (U.S. 4,813,973).
• An example of a suitable dye is dibenzosuberenol.
• Polymers were tagged by mixing the dye with polyacrylamide in a dilute aqueous solution with an acid catalyst at room temperature for 10 to 24 hours. The polymers were recovered by precipitation in methanol and analyzed spectrophotometrically. The process requires the dissolution of the polymer to be tagged in water and the polymer has to be acrylamide based.
• the invention comprises the N-substituted acrylamide polynuclear aromatic fluorescent dye: A. N-9-xanthenylacrylamide, or B. N-dibenzosuberenylacrylamide Systematic name: (N-5(5H-dibenzo[a,d]cycloheptenyl)acrylamide).
• the invention also comprises a water soluble vinyl polymer which contains at least one water soluble vinyl momomer and from 0.01 - 2.0 mole % of either of the two vinyl monomers, N-9-xanthenylacrylamide and N-dibenzosuberenylacrylamide.
• These water soluble vinyl polymers are preferably prepared by vinyl addition polymerization.
• the water soluble vinyl polymers that are modified using the acrylamide monomers N-9-xanthenylacrylamide and N-dibenzosuberenylacrylamide are those water soluble polymers prepared from the monomers acrylamide, acrylic acid and mixtures thereof.
• Water soluble cationic monomers can be modified in accordance with the teachings of the invention and are illustrated by such monomers as diallyldimethyl ammonium chloride and dimethylaminoethyl acrylate and diethyldimethylaminopropylmethacrylate.
• the amount of either monomer N-9-xanthenylacrylamide or N-dibenzosuberenylacrylamide that may be co-polymerized with the monomers described above will vary from as little as 0.01 up to -2 mole %. Since the novel acrylamide monomers of the invention are water soluble the amount used in preparing water soluble polymers should not be such as to reduce the solubility of the product sought to be tagged.
• the reaction media may be water, acetic acid, formic acid, or in water-acetic acid or water-formic acid mixtures.
• Preferred solvents contain from 5% to 90% acetic or formic acids.
• the reaction temperature is from 0°C to 40°C, preferably 10°C to 30°C.
• the acrylamide used was an aqueous 40% solution.
• the acrylamide was dissolved in the acetic acid, then the 9-hydroxyxanthene was added while stirring. The mixture was covered with foil and stirred for 48 hours. The product separated as a precipitate. The precipitate was filtered, washed with water and subsequently dried.
• Dibenzosuberenol was added with stirring into an acetic acid solution of acrylamide at room temperature.
• Monomer solution A was charged into a 300-ml Parr reactor.
• the solution was heated to 35°C and initiator solutions B and C were added into the monomer solution with stirring.
• the valves of the reactor were quickly closed.
• the reaction mixture was warmed up slowly and an exothermic reaction occurred at about 50°C and the temperature rose quickly to 135°C.
• the polymer was characterized by GPC using UV and fluorescence detectors. Results show the polymer was fluorescent.
• Monomer solution A was charged into a 300-ml Parr reactor.
• the solution was heated to 35°C and initiator solutions B and C were added into the monomer solution with stirring.
• the valves of the reactor were quickly closed.
• the reaction was highly exothermic and the temperature of reaction mixture rose quickly to about 140°C.
• the polymer was characterized by GPC using UV and fluorescence detectors. Results show the polymer was fluorescent.
• N-9-xanthenylacrylamide and N-dibenzosuberenylacrylamide monomers have been prepared and characterized by NMR and IR.
• the 9-xanthenylacrylamide group shows little fluorescence.
• the N-dibenzosuberenylacrylamide group shows strong fluorescence at 345 nm (ex 295 nm).
• Polyacrylic acid and poly(acrylic acid-acrylamide) prepared with 2 wt. % of N-dibenzosuberenylacrylamide comonomer show fluorescence at 345 nm and can be detected readily with fluorometer.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (6)

• 1991
  • 1991-03-21 ES ES91302466T patent/ES2074655T3/es not_active Expired - Lifetime
  • 1991-03-21 DE DE69109911T patent/DE69109911T2/de not_active Expired - Fee Related
  • 1991-03-21 EP EP91302466A patent/EP0449505B1/fr not_active Expired - Lifetime
  • 1991-03-22 AU AU73718/91A patent/AU641485B2/en not_active Ceased

Non-Patent Citations (3)

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